HabitStack Podcast

Bookkeeper, Controller, or CFO? How to Know Which One Your Business Needs

In this episode of the HabitStack Podcast, host Scott Ward sits down with Josh Leyenhorst, fractional CFO and founder of BasePoint, to break down the financial frameworks that help founders run smarter businesses. Josh breaks down the difference between bookkeeping, controller work, and CFO-level thinking, framing them as hindsight, insight, and foresight, and explains why even founders who think their books are clean often have messy data driving bad decisions. He introduces a reverse-engineering framework that starts with a founder's personal life goals across five areas (faith, family, fitness, fun, and finance), converts them into a monthly cash requirement, and works backward to determine exactly what the business must generate in revenue and which specific levers to pull to get there. Josh also unpacks a vested profit sharing model as an alternative to equity, explaining how it creates long-term employee alignment without giving away ownership or control, and explains why overpaying good people is often cheaper than losing them. He addresses financial shame directly, noting that many outwardly successful companies are quietly struggling, and why naming that reality is often the first step to fixing it. Tools from Josh Leyenhorst * https://www.basepoint.ca/tools [https://www.basepoint.ca/tools] * https://www.youtube.com/watch?v=c9kOU_dHoUU [https://www.youtube.com/watch?v=c9kOU_dHoUU]

Get Out of the Weeds: Laura Pitsch on Building a Business that Runs Smoothly

In this episode of the HabitStack Podcast, host Scott Ward interviews Laura Pitsch, a fractional COO who works with founder-led businesses navigating the messy middle between startup chaos and scalable operations. Laura explains why the $3 to $4M revenue range is where businesses most commonly stall and why founders who avoid investing in operational leadership rarely make it to the next level. She breaks down the real difference between an executive assistant, a chief of staff, and a COO, and why misunderstanding these roles leads to expensive mismatches. Laura shares her framework for helping founders get out of the day-to-day: identifying key functional leaders, assigning two to three accountability metrics per area, and running leadership meetings where real conversations actually happen. They also dig into feedback culture, why founders avoid it, why that avoidance compounds over time, and a simple daily habit that starts shifting the dynamic immediately. Laura also makes a case for doing fewer things better, and why throwing headcount at a messy operation just makes the mess more expensive.

Stop Being the Bottleneck: Keegan Sard on Delegation and Decision-Making

In this episode of the HabitStack Podcast, host Scott Ward interviews Keegan Sard, a fractional chief of staff based in Monaco who has been doing fractional work for 10 years. The conversation explores the critical difference between a chief of staff and a COO, and why chiefs of staff focus on the founder's priorities without P&L responsibility. They discuss why founders should hire fast and fire faster instead of endless interview rounds, and the distinction between executive assistants who manage calendars and chiefs of staff who make strategic decisions on the founder's behalf. Keegan explains decision playbooks for empowering teams without bottlenecking the founder, quick wins like eliminating payroll from the founder's plate and conducting calendar audits, and implementing the Ritz Carlton's $2,000 rule where every employee can spend money to fix problems without approval. They dive into why founders should include bad news in investor updates to get help before it's too late, the importance of listening tours in the first 90 days, and why anonymous feedback reveals customer insights that never make it up the chain.

B2B Storytelling and Team Empowerment: Alisa Manjarrez on Stories Bureau's Evolution

In this episode of the HabitStack Podcast, host Scott Ward interviews Alisa Manjarrez, managing director of Stories Bureau, a creative agency focused on B2B marketing and internal corporate storytelling through presentations, videos, and podcasts. Alisa shares what she's learning from Multipliers by Liz Wiseman about scaling herself as a leader. The conversation explores how Stories Bureau evolved from presentation design for market research professionals at companies like Mars Wrigley into narrative podcasts and video production. They discuss why small companies should ignore advice to be on every social platform and instead master one channel at a time, while leveraging the research behind Fortune 500 messaging strategies for their own audiences. Alisa explains why podcasting isn't going out of style despite the average podcast getting only 30 listens, how 1,000 listens puts you in the top 10%, and why podcasts are the new book as proof of expertise. Alisa shares how she's repositioning Stories Bureau to lead with relationship-driven partnership rather than just showcasing work like competitors.

Writing for Humans and Machines: Belinda DiGiambattista on Growing Good2bSocial

Scott Ward interviews Belinda DiGiambattista, CEO of Good2bSocial and founder of Choose Your Metric. Belinda shares her entrepreneurial journey from Fortune 500 financial services to building Butter Beans, a school lunch company she grew from zero to 5,000 lunches a day before selling in 2017, and how those lessons shaped her consulting work and eventual acquisition of Good2bSocial, a digital marketing agency serving the legal industry. The conversation explores Belinda's philosophy that every business needs one primary North Star metric that drives decisions and eliminates distraction. Belinda explains how her non-digital marketing background gives her a beginner's mind advantage, helping her team focus on actionable insights rather than raw data. They dive into leadership development through training, delegating with trust, and using mission, vision, and core values as a decision-making framework that scales culture without requiring the founder to be involved in everything.